The Happiest Days of Our Lives
by TheStigsWriterCousin
Summary: Dean is the class troublemaker at Lawrence High School. He's a pain in every teacher's ass and the epitome of a lost cause until his new History teacher takes an interest in him. Seeing himself in the young student, Castiel Novak makes it his mission to help Dean- If Dean will have him. Castiel/Dean, slash, teacher/student. Will be rated M. Somewhat slow burn.
1. Chapter 1

**A/N**: Just to prepare you all, this is going to be more of a slow burn than I am usually known for. It will eventually be rated M and I will update the rating when it gets there. Apologies in advance for John not being the Father of the Year in this one, we'll see if he is able to redeem himself by the end of the story.

The title of the story comes from an excellent, less well known Pink Floyd song that I think fits this story really well. Also, while Dean is not a child in this story, he is under 18 (much younger than a 33-ish year old Castiel) so keep that in mind if that is something that bothers you.

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Castiel looked around the room at all of the new faces, taking it all in before hushing the crowd. The school wasn't in his ideal neighborhood and the classroom was small and seemed ill-equipped, but he wasn't going to focus on that. He wasn't going to let anything bring him down now that he had finally realized his dream. "Good morning, everyone. I'm Mr. Novak, your new History teacher. I know it's a little late in the year to be getting a new teacher, but I'll try to make the transition as easy as possible for you all. Let's start with-"

The door slammed open loudly, grabbing everyone's attention. Castiel took in the sight of the student that startled him. He was gorgeous- Sandy brown hair and cheeks covered in light freckles that would probably darkened under the coming summer sun. His sleeves were rolled up, showing off toned arms and Castiel couldn't look away. Luckily for him, everyone was also staring, so his gaze wasn't out of place. "And who might you be?"

The student smiled brightly, his cockiness evident in the way that he looked Castiel up and down before responding. "Dean Winchester. What about you, babe?" He took a seat and propped his feet up on the chair in front of him.

The entire class snickered until Castiel shot them a firm glare. "My name is Mr. Novak and I'm your teacher, not your babe."

As Castiel turned to move back to his desk, he could have sworn he heard the boy mumble 'not yet', but he let it slide, choosing instead to pretend that he didn't hear it.

After settling into the lesson, Castiel considered calling Dean to stay after class to have a word with him, ultimately deciding against it. Clearly the boy thrived on attention and acknowledging that he had crossed a line would just feed his ego.

As the students packed up and filed out, Castiel called him over. "Mr. Winchester." He paused, waiting to see the response. Just as he thought, the eye roll he received told him that the boy had been expecting to be called out. "Have a good weekend."

Castiel held his smile until the students all left, extremely proud of himself for the confused look on Dean's face when he wished him well instead of scolding him. He kicked his feet up on the desk and soaked in the feeling of having completed his first day successfully. He was going to be really good at this.

Two weeks later and both Dean's tardiness and his flirting had become alarmingly normal. After calling Castiel 'babe' on the first day, Dean had only pushed the boundary, seemingly hopping to get in trouble.

_Castiel bent over to pick up his briefcase from the ground when he heard a low whistle from behind him. Turning around, he saw the last student still sitting at his desk, Dean Winchester. "Shouldn't you be heading home?"_

_ "Nah, I'm gonna stay a while- enjoy the view..." His smile widened when Castiel was unable to hide the pink across his cheeks. "Plus, there's no use leaving. Detention's in here today."_

_ "You don't have your homework from yesterday, Dean?" Castiel had made his way through the room and collected everyone's work except for Mr. Winchester's. He tried not to look too disappointed as bright green eyes looked up at him through dark lashes._

_ "Nah, I didn't feel like it." His posture straightened and his eyes narrowed slightly. "You could punish me, if you want..."_

_ Castiel walked away without batting an eye, but took a deep breath while his back was turned to his students._

Castiel had given him a quick word each time after class, but didn't want to give in, showing Dean that he was getting to him. This time, he couldn't let it slide.

"This weekend's assignment is optional." He paused for the round of applause that roared up at his words.**"However**, those of you that need the extra credit, this is not difficult so please do it. Have the assignment ready to turn in on Monday."

"You know, this isn't the kind of extra credit I had in mind..." When he looked up, he expected to see a grin or a smirk, not to see Dean licking his lips. He coughed as he tried to regain his composure.

"Mr. Winchester. After class." A hushed tone of 'oooh's made it around the room before the bell rang, silencing it.

When all of the students had gone, Castiel shut the door before making his way to Dean's desk. He propped himself up on the desk across the aisle and thought for a moment about what to say. "Mr. Winchester, why do you insist on making inappropriate comments in my class?"

"Don't flatter yourself, babe, I'm inappropriate in every class." Dean kicked his feet up, pushing Castiel's boundaries testing to see how much he can get away with.

"Why?" He refused to give into the student's goading. He looked at Dean without any anger or frustration in his eyes, hoping that Dean knew that he wasn't upset, just curious.

"Because this school is a joke. You should be glad I'm even here half the time." Castiel could tell that Dean's aloof attitude was staring to slip.

"What are you going to do after you graduate- IF you graduate?" He could see that he had struck a nerve in the boy with that one.

Den huffed, eye contact lost. "I don't need school, I'm gonna have to work for my dad anyway. The family business, you know..." Dean's eyes fell to the desk and he began picking at the edge of the wood.

"You don't have to do that if you don't want to, Dean." Castiel pulled the chair forward, sitting down closer to Dean. "You don't have to do anything you don't want to do."

Dean opened his mouth to speak, but when his eyes met Castiel's, he stopped.

Castiel sighed. He had gotten everything that Dean was willing to share with him. "You should do the assignment this weekend. It's easy and it will help your grade."

When he stood to leave, Dean looked surprised. "You're not gonna get me in trouble?" He had obviously never had a meeting with a teacher that hadn't ended in a detention sentence. "I mean, I have detention all next week anyway so it wouldn't matter anyway..." He pretended not to care, trying a little too hard to recover his attitude.

"Dean, I'm not here to punish you, I'm here to help you." He leaned in, making sure that he had Dean's full attention before continuing. Once the vibrant green eyes were locked with his, he spoke again. "If you ever need anything- Anything at all... I'm here."

Castiel saved them both the awkward silence to follow such a heavy statement by walking back to his desk to pack his things up. He didn't miss the way Dean paused at the door before pushing it open.

Monday was almost over and Castiel was almost too eager to see one single student in his final class of the day. In his head, Dean would come through the door on time, extra credit assignment complete, eager to turn his life around. Castiel knew he was dreaming to think that he could just come into a school and immediately change anyone's life, but he had to dream.

As the minutes ticked on, his last class began and his spirit fell with every minute that Dean didn't show up. When the final bell rang, Castiel absentmindedly dismissed his students, stuck in his own head about where Dean could have been. The click of the door as the final student left caught his attention and he stood suddenly with an idea.

Down the hall and a few doors later, he knocked on the door frame before stepping into the classroom. "Mr. Crowley?"

"Can I help you?" The man's thick accent did nothing to hide the fact that he was not in a good mood.

"Yes, I'm here for detention."

"And what did you do, love?"

Castiel stared blankly at him for a moment, considering his response before the man continued. "Lighten up, I'm kidding. So, they sent you here to watch the misfits, eh?"

"I told the Principal that I would take over duties for today."

"I must have missed the memo. Well, good luck then." The man wasted no time in packing his belongings, leaving Castiel alone in the room to await the students, hoping that Dean would show up even though he skipped class.

As usual, Dean was the last one in more than ten minutes after detention began. He kept his head down, but it didn't keep Castiel from noticing that his bottom lip was split and there was a slight shadow under his left eye.

Detention went by silently while Castiel contemplated what to say to Dean when it was over. He knew that it would be too easy too scare him away by coming on too strong and demanding to know what happened, but he felt an overwhelming need to know. As the bell rang, he noticed Dean sitting in his seat, not moving to leave.

He waited patiently, continuing to work on his lesson plan when he finally heard Dean's chair screech as he stood up. "Aren't you gonna ask me what I did?"

"Why would I assume you did anything?" Castiel tried to keep his expression normal, but Dean's tone saddened him.

"Everyone always assumes I did something wrong." Dean dropped his bag on the floor and propped himself against the desk, shoulders down. "Why should you be any different?"

Castiel sighed. "I'm more concerned if you're alright."

"It's not a big deal. Some guy was hassling my little brother..." Castiel could tell that he wasn't getting the whole truth, but he didn't press.

"Are you okay?"

"Yeah."

"Dean." Castiel waited until Dean was looking at him. "Are you okay?"

Dean's tongue ran across his lip as he nodded. "Yeah, I am." They sat in an uncomfortable silence for a few moments before Dean pulled out a paper out of his bag, placing it on the desk. "Thanks, Mr. Novak."

Castiel looked down at the page with a smile. Dean had done the extra credit assignment. He put the paper into his bag and resolved that tomorrow he was going to get Dean on the right path. He knew that with a little help, he could do well and he would be lying if he said that he wasn't excited at the chance to spend more time with Dean.

TBC


	2. Chapter 2

**A/N**: Warnings for this chapter include a non-descriptive mention of past self-harm. Please be aware of possible triggers.

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Dean walked out of the classroom, his footsteps echoing down the empty halls as he headed for the parking lot. He drove home in silence, baffled about what had just happened. He had expected to be lectured for missing class or for the teacher to have rolled his eyes, having not been surprised that Dean had gotten into another fight and missed another class.

But Mr. Novak wasn't angry with him or upset with him, he was concerned. No one had ever asked Dean if he was okay after a fight- No one but Sam.

After everything he had done, Mr. Novak hadn't lost his temper. He had never tried to embarrass Dean in front of the class or belittle him into behaving. Even though Dean had made more than a few inappropriate comments toward his teacher, he had been nothing but respectful back and Dean didn't know what to make of it.

Before stepping out of his car, he shook off the weird feelings. He figured that the guy was new and his patience would wear off eventually and then he would be like all the others that barely found it worth their time to even acknowledge Dean's presence. Then things would be back to normal.

Stepping through the door, he kicked his shoes off. "You home, Sammy?" Dean dropped his bag off by the door, heading into the house.

"Hey, Dean. Where have you been?" Sam was sitting at the kitchen table, papers spread out all around him.

"Stayed a little late after detention. No big deal. You hungry?"

"Yeah. There's just something about math that makes me really want food." Sam closed his books and put his pencil down.

"Well, I gotta run to the shop..." Dean pulled a twenty from his wallet and set it on the table in front of his brother. "Order a pizza or something. I won't be gone too long." He ruffled his brother's hair before bolting up the stairs. He had to get changed fast, he didn't have time to be bothered by Sam's nosy questions.

"But Dean, don't you have homework too?" Sam's question echoed down the hall, remaining unanswered as Dean came back downstairs in his worn-out jeans and old AC/DC shirt.

"You were supposed to be here at 5." Dean had only taken two steps into the building and he already heard his father's voice booming at him.

"Sorry, sir. One of my teachers wanted to talk to me, so I stayed late." Dean held his breath as he waited for his father's reply.

After considering the excuse, he replied. "Which teacher?" John Winchester had always been able to tell when his sons were lying to him, so he always made sure to get enough details when they started making excuses.

Dean wouldn't put it past him to call and check his alibi. "Mr. Novak. He's my new History teacher."

He stared at Dean, trying to discern if he was being honest. He must have been at least satisfied enough to drop it. "Don't let it happen again. You've got a stack of discharge forms and three new clients to get started on. I'm going home."

Dean nodded and began to look over the work that needed to be done as his father packed up his things for the day. It was only about an hours worth of paperwork, but then he had one oil change, a fuel pump replacement and a new set of brake pads.

It was a little after midnight when he finished cleaning his station, scrubbing his hands one last time before leaving. He never could get the last bit of grime from under his nails, but he didn't mind the grease residue. It had become something so normal to him that he almost didn't notice it.

The house was dark when he walked in, but he didn't need to see where he was going. The only light he needed was the one when he opened the fridge. He silently blessed his little brother for saving him three slices of his favorite triple meat pizza as he pulled the box out and sat down at the table.

He took a huge bite and his stomach growled in approval. He hadn't eaten since lunch and he was starving. As he went in for his second bite, he was startled when the light above him came on suddenly.

"What are you still doing up?" John leaned against the doorway, slightly red in the face and Dean could smell the booze on him from all the way across the room. He must have just gotten home from the bar.

"I just got home a few minutes ago-"

"Well, you better get on to bed. Got school real early tomorrow and you better not be late for work again." Dean could tell that his father wasn't in the mood to be questioned and his face wasn't ready for another round with the older man.

Dean looked down at the pizza in his hands as his stomach grumbled in protest as he reluctantly set it back in the box. "Yes, sir."

Luckily for Dean, he was as tired as he was hungry, falling into a deep sleep just shortly after his head hit the pillow. If he did dream, he didn't remember it. He had been blissfully unaware of everything until his alarm went off, blaring his favorite Asia song "Heat of the Moment" until he was wide awake.

He stumbled over to his brother's room, tapping lightly on the door in an attempt to wake Sam up without also waking their father. "I'm up..." A pathetic reply was barely heard through the wood, but it was good enough for Dean to head downstairs.

He could have gotten an extra twenty minutes of sleep, but his stomach was insisting that he eat before school and he wanted to make Sam something to take for lunch. He looked over to the trash can in the corner of the kitchen and he saw the pizza box sitting on top. He sighed as he opened the fridge, seeing nothing else that seemed nearly as good as that pizza would had been.

"Eww, gruel for breakfast?" Sam looked over to the pot of oats that Dean started stirring, skepticism clearly written on his face.

"Dude, it's oatmeal. I'll put a ton of sugar in it, don't worry." Dean seasoned then portioned it out and they sat down to eat. "Your lunch is in your bag."

"Thanks, Dean." Sam made an oddly accepting face as he ate the oatmeal, surprised at the fact that it tasted much better than it looked. "Oh! You don't have to give me a ride today, I'm gonna walk with Barry."

"Cool. What about after school?"

"Same. You gonna work tonight?" They kept chatting as they cleaned up before heading out the door.

"Yeah, I don't want to get behind.." Last time Dean had skipped a day of work, he missed the next day of class because he was at the shop until almost four in the morning making up for the work that his father hadn't done.

"K. See you later."

Dean smiled and waved as his brother walked off with his friend. Sam was a good kid and was pretty much the only thing keeping Dean from running away.

Dean didn't bother even trying to pretend that he was paying attention throughout the day- he was so tired. By the end of the day, all he wanted to do was take a nap in his car, but his last class was Mr. Novak and if he had to see those crystal blue eyes staring at him like a disappointed puppy, he would die.

He had managed to make it to his final class, but he struggled to stay awake. Before he knew it, he heard his name being called. "Mr. Winchester..." His head snapped up as he heard a deep voice beckoning him. He looked around the room, noticing that it was empty except for his teacher.

"Huh?" He was disoriented, trying to look anywhere but at Mr. Novak, who was too close, with his hand resting on Dean's shoulder.

"It's time to get up. You need to get to detention, don't you?"

Dean rubbed his eyes, looking up at the clock. His teacher was right, he only had a couple of minutes to get to the room before they would lock the door on him. "Thanks."

"When you're done with detention, I'd like for you to meet me at the principal's office."

Dean grabbed his bag and shifted uncomfortably on his feet. His stomach twisted into a knot as he considered asking why. If Mr. Novak had finally given up on him, he didn't want to know so he nodded. "Okay."

He slept through detention without any problems, the teacher preferring to ignore the kids as long as they kept quiet until the timer went off. The sound of restless students woke him a few minutes before their time was up. Looking around the room, he could tell that everyone was starting to lose their patience waiting for four o'clock.

"Ugh, just go." The teacher sighed, obviously not wanting to deal with them for the last few minutes of detention. After they fought for the door, Dean's stomach knotted as he made his way to the Principal's office.

"Mr. Novak, I know you're new here, so you don't know any better yet..." Dean stood outside the door, not intending to overhear the conversation, but not wanting to interrupt it either. "But there are some students that just aren't worth your time."

"Principal Roman, I hardly think that's appropriate to say about any of our students." Dean recognized the gruff voice as Mr. Novak immediately. Were they talking about him?

"Appropriate or not, it's the truth. Dean Winchester is a lost cause." Dean's fists clenched his jeans as he listened to the Principal speak. He knew what people thought about him, but it was harder to hear it first hand. "I won't allow you to waste school resources-"

"Principal Roman!" Dean jolted back from the door as he hear his teacher's voice raised like never before. "I will make this very clear for you: I don't care what you think about my students, but you are required, as their Principal, to do everything in your power to help them succeed. If you do not sign this paper, I will report you to every advisory board that I can find and I will not stop until you're fired."

Dean held his breath as a heavy silence came over the room. He considered leaving, but couldn't bring himself to move before the door was flung open in front of him. He stood face to face with Mr. Novak, who was red in the face from his encounter with Principal Roman.

"Dean." He wanted to look away, not wanting to look Mr. Novak in the eyes after what he had just heard, but he couldn't. The soft look in his teacher's eyes was something that he had never seen before. "Come to my room, please."

They walked in silence, Dean sitting on top of a table rather than in the seat, not feeling comfortable enough to settle in as he waited for his teacher to speak.

"I'm sorry that you had to hear that..." The older man pulled up his chair, sitting in front of Dean. "The meeting didn't go how I planned."

"What exactly did you have planned?" Dean looked over to him, confusion clear in his face. He waited for a reply, but instead was handed a piece of paper to read. "What is this?"

"It's an agreement. You're excused from detention for the rest of the year. In exchange, you will come to my class for private tutoring."

Dean looked back down at it, noticing the Principal's signature at the bottom. "I can't believe Principal Dick signed this." Dean knew all too well how much the Principal wanted a reason to expel him, so for the man to actually sign a document to help Dean wasn't something that he could have anticipated.

"Well, he didn't want to." For the first time, Dean was seeing his teacher angry, but it wasn't directed at him. "Don't tell anyone I said this, but that guy's an asshole."

Dean chuckled a little before handing the paper back over to Mr. Novak. "Why are you doing this?"

"Because I believe in you, Dean."

Dean searched his face looking for any sign of deceit or ulterior motives, coming up empty handed. "You're the only one." He looked away, embarrassed by the fact that his eyes were beginning to tear up.

"Can I show you something?" Dean blinked a few times and cleared his throat before speaking.

"Sure."

He stared at his teacher, not missing how nervous he suddenly looked. He was about to ask what it was that he was being shown when Mr. Novak started to unbuckle his watch band. He rubbed his wrist a little before rolling his sleeve up to show Dean his exposed skin.

"When I was 19, I tried to kill myself." Dean's heart stopped for a moment as he looked at the raised pink scar that ran across his teacher's wrist. When he looked up into Mr. Novak's eyes, they seemed darker than normal.

"Why?"

"I was alone. I grew up an orphan- no one wanted me. I was placed with a lot of families, but they didn't want to keep me. Some of them told me up front that I was worthless... Some of them were nice, but in the end, I wasn't good enough for them."

Dean stayed silent, listening to the unbelievable story. How could someone as nice as Mr. Novak have been through that?

"When I turned 18, I aged out of the system. They have programs that are supposed to help kids find work and housing before then, but it didn't work out for me. I spent a year living on the streets before I couldn't stand it anymore. I felt like there was no reason for me to live."

He could see the far-off look in his teacher's eyes as he told the story, part of him reliving it as he spoke.

"After I did it, I woke up in a church with a bandage on my wrist. That's where I met Pastor Jim." Dean was relieved to see his teacher smile. "He saved me- he believed in me when no one else did, myself included. He gave me a purpose and he helped me realize that I could be so much more than I was."

"He told me 'A man is not his circumstances, for both a man and his circumstances can change'." Mr. Novak looked him right in the eyes. "Not many people know about my past, Dean..."

"Why are you telling me about it?"

"Because I want you to know that I understand. I know how it feels to be told you're worthless- that you're a lost cause. I know what it's like to not be able to see the light at the end of the tunnel. You put up a good front, but I've been there. I know how hard it is to keep that front up and I know how it ends when it becomes too difficult."

Dean looked down at his own hand, unconsciously rubbing his wrist. "I wouldn't-"

"I know! I know... I'm not saying that you would, I just... I want to help you. I know that you're capable of so much more than what everyone thinks."

He felt a burning in his eyes again as his teacher's words sunk in. If he didn't have Sammy to think about, would he end up like that? So hopeless that he would want to end his life? Part of him knew that it was a possibility and it scared him.

"What if I'm not?" His eyes were wet, but he blinked, trying to keep himself calm, at least on the outside.

"If you don't try you'll never know." Mr. Novak stood, looking down at him with pleading eyes. "I want to help you, but I can't do it for you. You have to want it- to prove them all wrong." His teacher held his hand out, waiting for Dean to join him. "Your future is worth fighting for. Are you in?"

Dean nodded and smiled a little as he reached out to shake Mr. Novak's hand. He was surprised when the older man pulled him forward, his other hand gripping Dean in a tight hug. After a moment of uncertainty, he let himself relax into the embrace.

Dean had spent his entire life being the one to take care of his brother and father, he had almost forgotten what it felt like to be looked after. He had become so used to it that he hadn't realized how alone he had felt until then. "It's going to be okay." He nodded against the warmth of Mr. Novak's chest as a feeling of relief washed over him.

TBC


End file.
